Shelter Island, NY Homes

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  $4,250,000

  • 4 Beds
  • 5 Baths
  • 3,676 Sq Ft

  8 Cove Way, Shelter Island, NY 11964

  Enviably located on Shelter Island's southern coast with 113' of waterfront on Menantic Creek, this half-acre property was fully reimagined in a high-end 2017 renovation that left no detail overlooked. Offering 3,676 +/- sq. ft. across 2 levels, the home includes 4 bedrooms, 5 baths, 2 fireplaces, a heated gunite pool, outdoor kitchen, firepit, specimen gardens, and a private deep-water dock. A

  Stacey Cohen Saunders & Associates

  8 Cove Way, Shelter Island, NY 11964
• Explore Shelter Island

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  /26

  $14,400 per month

  • 4 Beds
  • 2 Baths
  • 2,669 Sq Ft
  • Property for Rent

  12 Dogwood Ln, Shelter Island, NY 11964

  Discover the perfect island getaway in this spacious 4-bedroom, 2-bathroom home tucked away on a large, serene lot. Surrounded by mature landscaping, the property features a generous front porch overlooking a peaceful pond—an ideal spot for morning coffee or sunset relaxation. Inside, the home offers a bright and inviting layout with a well-appointed kitchen complete with a center island, perfect

  Mackenzie Needham Daniel Gale Sothebys Intl Rlty

  12 Dogwood Ln, Shelter Island, NY 11964
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  $975,000 Sold May 20, 2025

  1 Rebel Rd, Shelter Island, NY 11964

  • 2 Beds
  • 2 Baths
  • 1,472 Sq Ft
  • Built 1981

  Last Sold Summary

  • 20% Below List Price
  • $662/SF
  • 174 Days On Market

  Current Estimated Value $1,218,000

  Last Listing Agent Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  1 Rebel Rd, Shelter Island, NY 11964
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  Est $2,145,000 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,628 Sq Ft

  45 New York Ave, Shelter Island, NY 11964

  45 New York Ave, Shelter Island, NY 11964
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  /23

  $2,999,000

  • 3 Beds
  • 2 Baths
  • 1,373 Sq Ft

  13 Tarkettle Rd, Shelter Island, NY 11964

  Nestled on a 1.08 acre lot along Shelter Island’s coveted Dickerson Creek, this Scandinavian-style waterfront cottage embodies quintessential Hamptons elegance with 100 feet of picturesque shoreline and a sparkling pool.Inside, a light-filled and inviting floor plan features three bedrooms and two newly updated bathrooms, designed for modern comfort. The stylishly renovated kitchen is sure to

  Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

  13 Tarkettle Rd, Shelter Island, NY 11964
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  $7,500 per month

  • 4 Beds
  • 2.5 Baths
  • 2,825 Sq Ft
  • House for Rent

  42 N Menantic Rd, Shelter Island, NY 11964

  Escape to Tranquility Base, a light-filled modern retreat where timeless mid-century style meets today’s elevated comforts. Thoughtfully renovated and expanded, this 4-bedroom, 2.5-bath home is surrounded by lush, landscaped grounds and designed for seamless indoor–outdoor living—thanks to five sliding glass doors that open to a heated gunite pool and expansive entertaining deck.Enjoy the

  Jeanmarie Bay William Raveis New York LLC

  42 N Menantic Rd, Shelter Island, NY 11964
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  $2,679,000 Sold Jan 21, 2026

  156 Ram Island Dr, Shelter Island, NY 11964

  • 4 Beds
  • 4 Baths
  • 3,420 Sq Ft
  • Built 1995

  Last Sold Summary

  • 36% Below List Price
  • $783/SF
  • 446 Days On Market

  Last Listing Agent Mary Elizabeth Galle Corcoran

  156 Ram Island Dr, Shelter Island, NY 11964
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  Est $1,577,830 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,637 Sq Ft

  16 Great Circle Dr, Shelter Island, NY 11964

  16 Great Circle Dr, Shelter Island, NY 11964
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  $2,675,000

  • 4 Beds
  • 3 Baths

  55 Peconic Ave, Shelter Island, NY 11964

  Welcome to 55 Peconic Avenue, a bold, newly built statement home completed in 2022 and set on an expansive 1.4-acre parcel in one of Shelter Island's most coveted locations. Designed for true year-round living, this residence captures southwest-facing water views, dramatic light, and a seamless indoor-outdoor lifestyle that today's buyers demand. The main level delivers a clean, open-concept

  Jack Richardson SERHANT.

  55 Peconic Ave, Shelter Island, NY 11964
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  $63,000 per month

  • 3 Beds
  • 2 Baths
  • 1,487 Sq Ft
  • House for Rent

  4 Ivy Place, Shelter Island, NY 11964

  Located in Hay Beach, this year round furnished rental is available and fully furnished. 3 bedrooms and 2 full baths is located in the beautiful area of Hay Beach, just 2 minutes from Gardiners Bay Country Club. Large living room with fireplace and sliders out to the large awning covered deck. Large loft area off the living room could serve as an office area of for overflow guests.

  Sheri Winter Parker Corcoran

  4 Ivy Place, Shelter Island, NY 11964
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  $1,950,000 Sold Mar 14, 2025

  3 Sea Gull Rd, Shelter Island, NY 11964

  • 3 Beds
  • 2.5 Baths
  • 1,650 Sq Ft
  • Built 1953

  Last Sold Summary

  • 1% Below List Price
  • $1,182/SF
  • 322 Days On Market

  Current Estimated Value $2,969,025

  Last Listing Agent Cynthia Barrett Brown Harris Stevens Hamptons

  3 Sea Gull Rd, Shelter Island, NY 11964
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  Est $2,826,000 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,450 Sq Ft

  6 Behringer Ln, Shelter Island, NY 11964

  6 Behringer Ln, Shelter Island, NY 11964
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  $3,850,000

  • 4 Beds
  • 5.5 Baths
  • 3,985 Sq Ft

  8 Hilo Dr, Shelter Island, NY 11964

  This newly constructed modern residence offers stunning south-facing water views over West Neck Bay in Shelter Island. Thoughtfully designed to maximize its prime setting, the home spans approximately 3,985 square feet and features 4 ensuite bedrooms and 5.5 bathrooms, providing exceptional comfort and privacy. The interiors showcase a high level of craftsmanship and attention to detail,

  Enzo Morabito Douglas Elliman Real Estate

  8 Hilo Dr, Shelter Island, NY 11964
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  $75,000 per month

  • 6 Beds
  • 4.5 Baths
  • 4,600 Sq Ft
  • House for Rent

  15 Montclair Ave, Shelter Island, NY 11964

  Enjoy all The Hamptons have to offer in this newly recreated waterfront home in the heart of West Neck Harbor! Complete with a boat and complimentary captain at the end of your private dock. Every detail was masterfully thought through by a leading design team. The floor plan offers a first-floor primary suite, four additional private guest bedrooms with two gracious common living spaces, a

  Margot Reutter Corcoran

  15 Montclair Ave, Shelter Island, NY 11964
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  $795,000 Sold Oct 10, 2025

  33B S Midway Rd, Shelter Island, NY 11964

  • 2 Beds
  • 2 Baths
  • Built 1950

  Last Sold Summary

  • 11% Below List Price
  • 142 Days On Market

  Current Estimated Value $751,034

  Last Listing Agent Shane Donahue The Agency Hamptons

  33B S Midway Rd, Shelter Island, NY 11964
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  Est $2,666,349 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,200 Sq Ft

  Unlisted Address

  Unlisted Address
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  $3,750,000

  • 4 Beds
  • 3 Baths
  • 2,200 Sq Ft

  52 S Midway Rd, Shelter Island, NY 11964

  Around the bend from Turkem's Rest and a short paddle from Salt and Shipwreck, this recently renovated, 4-bedroom, circa 1908 Shelter Island farmhouse, on a shy acre, is perched above Menantic Creek with a substantial dock and profits from panoramic water views with southwestern exposure for magical sunsets. Wide waterfront vistas unfold across beautiful landscaping by Marders, broad greens lined

  Shane Donahue The Agency Hamptons

  52 S Midway Rd, Shelter Island, NY 11964
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  $2,650,000 Sold Oct 16, 2025

  7 Gazon Rd, Shelter Island, NY 11964

  • 3 Beds
  • 2.5 Baths
  • 1,901 Sq Ft
  • Built 1955

  Last Sold Summary

  • 8% Below List Price
  • $1,394/SF
  • 130 Days On Market

  Current Estimated Value $2,653,306

  Last Listing Agent Terry Thompson Douglas Elliman Real Estate

  7 Gazon Rd, Shelter Island, NY 11964
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  Est $1,181,694 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,726 Sq Ft

  105 S Ferry Rd, Shelter Island, NY 11964

  105 S Ferry Rd, Shelter Island, NY 11964
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  $4,445,000

  • 6 Beds
  • 8 Baths
  • 5,622 Sq Ft

  100 S Ferry Rd, Shelter Island, NY 11964

  A buyers dream rooted in nature, enhanced by design. This modern farmhouse nestled in the heart of Shelter Island, NY. completed in 2024, sits on a generous 2.16 acres of immaculate grounds, is a mere half mile from the South Ferry, placing convenience at your doorstep.Boasting six bedrooms, each with their own en-suite, and two additional half-baths, this residence effortlessly blends style

  Christine Beckwith Douglas Elliman Real Estate

  100 S Ferry Rd, Shelter Island, NY 11964
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  $1,450,000 Sold May 30, 2025

  5 Wade Rd, Shelter Island, NY 11964

  • 3 Beds
  • 3 Baths
  • 1,854 Sq Ft
  • Built 1967

  Last Sold Summary

  • 3% Below List Price
  • $782/SF
  • 20 Days On Market

  Current Estimated Value $1,482,559

  Last Listing Agent Rosanna Piazza Signature Premier Properties

  5 Wade Rd, Shelter Island, NY 11964
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  Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,800 Sq Ft

  8 Crescent Way, Shelter Island, NY 11964

  8 Crescent Way, Shelter Island, NY 11964
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  $2,650,000

  • 6 Beds
  • 4 Baths
  • 2,418 Sq Ft

  14 Freds Ln, Shelter Island, NY 11964

  Tucked away on a shy acre, this private retreat features a heated Gunite pool, fire-pit seating area, all framed by mature trees. The main house has an open floor plan with cathedral ceilings and exposed wood beams in the living room, a cook's kitchen with stainless steel appliances, island seating for 3-4, and a dining area that flows easily for entertaining. A deck off the kitchen sets the

  Melina Wein M WEIN REALTY INC

  14 Freds Ln, Shelter Island, NY 11964
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  $4,350,000 Sold Oct 31, 2025

  7 Westmoreland Dr, Shelter Island, NY 11964

  • 6 Beds
  • 4.5 Baths
  • 4,957 Sq Ft
  • Built 1901

  Last Sold Summary

  • 1% Above List Price
  • $878/SF
  • 18 Days On Market

  Last Listing Agent Carl Gambino Compass Greater NY LLC

  7 Westmoreland Dr, Shelter Island, NY 11964
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  Est $1,443,000 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,794 Sq Ft

  79A N Midway Rd, Shelter Island, NY 11964

  79A N Midway Rd, Shelter Island, NY 11964
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  $4,479,000

  • 4 Beds
  • 4.5 Baths

  70 Peconic Ave, Shelter Island, NY 11964

  Introducing 70 Peconic Avenue-an irreplaceable, one-of-a-kind waterfront estate commanding sweeping southwest views across the Peconic toward Southampton. With four fully finished levels, nearly every room framed by water, and private shoreline access, this is the kind of property that simply does not come back to market. From the moment you enter the front foyer, the view stops you in your

  Jack Richardson SERHANT.

  70 Peconic Ave, Shelter Island, NY 11964
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  $4,950,000 Sold May 30, 2025

  104 S Ferry Rd, Shelter Island, NY 11964

  • 5 Beds
  • 5.5 Baths
  • 4,040 Sq Ft
  • Built 2023

  Last Sold Summary

  • $1,225/SF
  • 14 Days On Market

  Current Estimated Value $4,779,436

  Last Listing Agent Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  104 S Ferry Rd, Shelter Island, NY 11964
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  Est $767,689 Not Listed For Sale

  3 N Cartwright Rd, Shelter Island, NY 11964

  3 N Cartwright Rd, Shelter Island, NY 11964
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  $1,035,000

  • 3 Beds
  • 2 Baths

  26 Ole Buck Run, Shelter Island, NY 11964

  ***NEW PRICE*** This recently renovated 3 bedroom, 2 bath home with wood burning fireplace is situated on .89 private acres. The home now has a: new roof, siding, and air conditioners. Newly refinished floors and painted interior. New back decks and exterior basement entry. Full basement with a walkout makes for a possible fourth ensuite bedroom. Adjacent to the 14 acre Westmoreland Farm Open

  Angelo Piccozzi DERING HARBOR REAL ESTATE LLC

  26 Ole Buck Run, Shelter Island, NY 11964
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  $2,799,000 Sold Nov 14, 2025

  12 Terry Dr, Shelter Island, NY 11964

  • 5 Beds
  • 4.5 Baths
  • 4,200 Sq Ft
  • Built 2015

  Last Sold Summary

  • $666/SF
  • 24 Days On Market

  Current Estimated Value $1,917,000

  Last Listing Agent Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  12 Terry Dr, Shelter Island, NY 11964
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  Est $1,510,829 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,460 Sq Ft

  1 Deer Park Ln, Shelter Island, NY 11964

  1 Deer Park Ln, Shelter Island, NY 11964
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  $1,375,000

  • 3 Beds
  • 2 Baths
  • 1,575 Sq Ft

  20 Crescent Way, Shelter Island, NY 11964

  This lovely home is nicely sited ona shy acre close to Menhaden LaneBeach and Golf. Hard wood floors throughout.Spaciousliving room with cathedral ceiling, fireplace andsliders which open onto a large deck and yard beyond. Three nice sized bedrooms, two full baths, formal dining room, chef's kitchen with gas stove, Den/potential media roomwith egress, two-car garage+.Yard is fenced with plenty of

  Melina Wein M WEIN REALTY INC

  20 Crescent Way, Shelter Island, NY 11964
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  $660,000 Sold Dec 02, 2025

  8 Wheeler Rd, Shelter Island, NY 11964

  • Land
  • 1.2 Acres
  • $550,000 per Acre

  Last Sold Summary

  • 17% Below List Price
  • 99 Days On Market

  Last Listing Agent Nicholas Planamento William Raveis New York LLC

  8 Wheeler Rd, Shelter Island, NY 11964
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  Est $2,333,619 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,774 Sq Ft

  18 Dickerson Dr, Shelter Island, NY 11786

  18 Dickerson Dr, Shelter Island, NY 11786
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  $1,300,000

  • 2 Beds
  • 2 Baths
  • 1,320 Sq Ft

  1 Meadow Place, Shelter Island, NY 11964

  Nestled off the road for added privacy this updated home offers Chase Creek water views. Featuring 2 bedrooms and 2 renovated bathrooms, the layout includes an office perfect for remote work or creative pursuits. The open-concept living and dining area is bright and inviting, flowing into the renovated kitchen with modern finishes and storage. Step out onto the back deck thru sliders from the

  Melina Wein M WEIN REALTY INC

  1 Meadow Place, Shelter Island, NY 11964
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  $1,725,000 Sold Jan 14, 2026

  27 Country Club Dr, Shelter Island, NY 11964

  • 3 Beds
  • 2 Baths
  • 3,170 Sq Ft
  • Built 2011

  Last Sold Summary

  • 13% Below List Price
  • $544/SF
  • 221 Days On Market

  Last Listing Agent Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

  27 Country Club Dr, Shelter Island, NY 11964
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  Est $865,000 Not Listed For Sale

  169 N Ferry Rd, Shelter Island, NY 11964

  169 N Ferry Rd, Shelter Island, NY 11964
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  $1,095,000

  • Land
  • 0.64 Acre
  • $1,710,938 per Acre

  12 Hilo Dr, Shelter Island, NY 11964

  .64 Acres on Shelter Island, adjacent to cumminty dock. Room fof house and pool

  Brian Buckhout Compass

  12 Hilo Dr, Shelter Island, NY 11964
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  Est $1,580,543 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,380 Sq Ft

  5 Country Club Dr, Shelter Island, NY 11964

  5 Country Club Dr, Shelter Island, NY 11964
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  $1,895,000

  • 4 Beds
  • 3 Baths
  • 2,296 Sq Ft

  73 N Midway Rd, Shelter Island, NY 11964

  A thoughtfully designed retreat offering peace, privacy, and understated luxury.Tucked away on a private drive in the island's center, you're close enough to bike to all of the island’s beaches or restaurants.The approach sets the tone: a winding drive reveals the house gradually. The home emerges across an expansive lawn, its clean black lines and Anderson windows throughout creating a

  JoAnn Wind Daniel Gale Sothebys Intl Rlty

  73 N Midway Rd, Shelter Island, NY 11964

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